EP2328862B1 - Diamide enthaltendes produkt, verfahren zu dessen herstellung und anwendungen davon - Google Patents
Diamide enthaltendes produkt, verfahren zu dessen herstellung und anwendungen davon Download PDFInfo
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- EP2328862B1 EP2328862B1 EP09783247.1A EP09783247A EP2328862B1 EP 2328862 B1 EP2328862 B1 EP 2328862B1 EP 09783247 A EP09783247 A EP 09783247A EP 2328862 B1 EP2328862 B1 EP 2328862B1
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- 238000000034 method Methods 0.000 title claims description 20
- 150000001470 diamides Chemical class 0.000 title claims description 13
- 239000000203 mixture Substances 0.000 claims description 141
- 238000009472 formulation Methods 0.000 claims description 90
- 150000001875 compounds Chemical class 0.000 claims description 81
- 239000002904 solvent Substances 0.000 claims description 53
- -1 propyl (n-propyl) Chemical group 0.000 claims description 30
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 238000004140 cleaning Methods 0.000 claims description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 239000005977 Ethylene Substances 0.000 claims description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 5
- 238000002844 melting Methods 0.000 claims description 5
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 4
- 238000005238 degreasing Methods 0.000 claims description 4
- 239000004014 plasticizer Substances 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- 239000008199 coating composition Substances 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims description 2
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- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
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- 239000013078 crystal Substances 0.000 description 20
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- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 17
- YDGMGEXADBMOMJ-LURJTMIESA-N N(g)-dimethylarginine Chemical compound CN(C)C(\N)=N\CCC[C@H](N)C(O)=O YDGMGEXADBMOMJ-LURJTMIESA-N 0.000 description 16
- YDGMGEXADBMOMJ-UHFFFAOYSA-N asymmetrical dimethylarginine Natural products CN(C)C(N)=NCCCC(N)C(O)=O YDGMGEXADBMOMJ-UHFFFAOYSA-N 0.000 description 16
- 150000005690 diesters Chemical class 0.000 description 16
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- 125000000217 alkyl group Chemical group 0.000 description 14
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
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- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
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- 238000002360 preparation method Methods 0.000 description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 9
- 239000001361 adipic acid Substances 0.000 description 8
- 235000011037 adipic acid Nutrition 0.000 description 8
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 8
- 238000010790 dilution Methods 0.000 description 8
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- 239000005906 Imidacloprid Substances 0.000 description 7
- 229910019142 PO4 Inorganic materials 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 229940056881 imidacloprid Drugs 0.000 description 7
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 description 7
- 235000021317 phosphate Nutrition 0.000 description 7
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- 125000004432 carbon atom Chemical group C* 0.000 description 6
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 6
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- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- BQYJATMQXGBDHF-UHFFFAOYSA-N difenoconazole Chemical compound O1C(C)COC1(C=1C(=CC(OC=2C=CC(Cl)=CC=2)=CC=1)Cl)CN1N=CN=C1 BQYJATMQXGBDHF-UHFFFAOYSA-N 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
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- 150000004665 fatty acids Chemical class 0.000 description 6
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- 239000004615 ingredient Substances 0.000 description 6
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- 229920006395 saturated elastomer Polymers 0.000 description 6
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 6
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 5
- 239000005944 Chlorpyrifos Substances 0.000 description 5
- 239000005947 Dimethoate Substances 0.000 description 5
- 239000005590 Oxyfluorfen Substances 0.000 description 5
- OQMBBFQZGJFLBU-UHFFFAOYSA-N Oxyfluorfen Chemical compound C1=C([N+]([O-])=O)C(OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 OQMBBFQZGJFLBU-UHFFFAOYSA-N 0.000 description 5
- 239000005591 Pendimethalin Substances 0.000 description 5
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 5
- 239000000417 fungicide Substances 0.000 description 5
- 239000004530 micro-emulsion Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 5
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 5
- 235000011044 succinic acid Nutrition 0.000 description 5
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 5
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
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- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 4
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- SFJOBYZKUSLNIG-UHFFFAOYSA-N 2,3,4-tris(1-phenylethyl)phenol Chemical class C=1C=C(O)C(C(C)C=2C=CC=CC=2)=C(C(C)C=2C=CC=CC=2)C=1C(C)C1=CC=CC=C1 SFJOBYZKUSLNIG-UHFFFAOYSA-N 0.000 description 3
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- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 101150093826 par1 gene Proteins 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- IBSNKSODLGJUMQ-SDNWHVSQSA-N picoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC(C(F)(F)F)=N1 IBSNKSODLGJUMQ-SDNWHVSQSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 description 1
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical class NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000011275 tar sand Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
- C11D7/5004—Organic solvents
- C11D7/5013—Organic solvents containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/05—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/20—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/033—Printing inks characterised by features other than the chemical nature of the binder characterised by the solvent
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/20—Diluents or solvents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/43—Thickening agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/16—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
- C10M133/56—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/32—Amides; Substituted amides
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/43—Solvents
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/32—Organic compounds containing nitrogen
- C11D7/3263—Amides or imides
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
- C11D7/5036—Azeotropic mixtures containing halogenated solvents
- C11D7/5068—Mixtures of halogenated and non-halogenated solvents
- C11D7/5095—Mixtures including solvents containing other heteroatoms than oxygen, e.g. nitriles, amides, nitroalkanes, siloxanes or thioethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/08—Amides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/28—Amides; Imides
Definitions
- the present invention relates to novel products comprising diamide compounds, uses of the products and at least one method of preparation. These products can in particular be used as solvents, for example in phytosanitary formulations.
- solvents are used for the formulation of phytosanitary assets, especially in the form of emulsifiable concentrates (Emulsifiable Concentrate "EC") intended to be diluted in water by the farmer, before application to a field.
- EC emulsifiable Concentrate
- the industry is looking for new products to vary or optimize products and processes in which solvents, including polar solvents, are to be used.
- solvents including polar solvents
- the industry needs low cost compounds with interesting properties of use.
- the industry also needs compounds with a toxicological and / or ecological profile perceived as favorable, in particular low volatility (low VOC), good biodegradability, low toxicity and / or low hazard.
- dialkylamides The use as solvents of dialkylamides is known. It is a product of formula R-CONMe 2 or R is a hydrocarbon group such as an alkyl, typically C 6 -C 30 . Such products are in particular marketed under the name Genagen® by the company Clariant. These solvents find applications particularly in the phytosanitary field.
- the diesters of dicarboxylic acids are also known as solvents, in particular the diesters obtained by esterification of a mixture of adipic acid, glutaric acid and succinic acid.
- solvents such products are marketed under the names Rhodiasolv® RPDE and Rhodiasovl® DIB by Rhodia.
- the document US 4588833 describes the preparation of substituted succinic acid amides.
- This document describes in particular the preparation of compounds of XOC-CH 2 -CHR 6 -CONEt 2 type where R 6 is a methyl or an ethyl.
- the products are prepared by bringing CO, an alcohol or an amine HX, and crotonic acid dialkylamide or pent-3-enoic acid diethylamide.
- the document teaches the use of the compounds as anti-oxidants, as stabilizers for plastics, or as organic synthesis intermediates.
- mixtures or combinations can be liquid while the components are individually solid.
- the invention also relates to a process for preparing the product of the invention.
- the invention also relates to the use of the product of the invention in formulations.
- the invention also relates to a process for preparing the formulations by adding the product of the invention.
- the invention also relates to formulations comprising the product of the invention.
- the formulations may in particular be phytosanitary formulations.
- the invention also relates to the use of the product of the invention as solvent, plasticizer, or coalescing agent.
- solvent is understood in a broad sense, covering in particular the co-solvent functions, crystallization inhibitor, stripper.
- solvent can in particular designate a liquid product at the temperature of use, preferably having a melting point of less than or equal to 20 ° C., preferably at 5 ° C., preferably at 0 ° C., which can contribute to making liquid a liquid. solid material, or to prevent or retard the solidification or crystallization of material in a liquid medium.
- a compound corresponding to a chemical formula means any compound responding to said. It is mentioned that the term "compound” also covers mixtures of several molecules corresponding to the same formula. It can therefore be a molecule of said formula, or a mixture of several molecules corresponding to said formula.
- a compound of formula (Ia) may be a molecule of formula (Ia) with defined groups R 2 , R 3 , R 4 and R 5 , or a mixture of several molecules corresponding to formula (Ia), said molecules having between them differences as regards the groups R 2 , R 3 , R 4 and R 5
- composition of matter means a composition, more or less complex, comprising several chemical compounds. It can typically be an unpurified or modestly purified reaction product.
- the compound of the invention may in particular be isolated and / or marketed and / or used in the form of a composition of matter comprising it.
- the product of the invention is a composition of matter.
- all the compounds of formulas (Ia), (Ib) and (Ic) may represent at least 10% by weight. Preferably, all of these compounds constitute the main product of the composition of matter.
- main product in the present application, the product whose content is the highest, even if its content is less than 50% by weight (for example in a mixture of 40% of A, 30% of B, and 30% of C, product A is the product main).
- all the compounds of formulas (Ia), (Ib) and (Ic) represent at least 50% by weight of the composition of matter, for example from 70 to 95% by weight, and even 75 to 90% by weight.
- the product may comprise at least two of the compounds of formulas (Ia), (Ib) and (Ic). It preferably comprises the three compounds.
- a a , A b , and A c are linear divalent alkyl groups, each comprising a different number of carbon atoms.
- Groups A a, A b and A c correspond to the diacids of formula HOOC-A-COOH, HOOC-A-COOH b, and c HOOC-A-COOH.
- the mixture of the compounds in these proportions can correspond (in amide version) to a mixture of Adipic, Glutaric and Succinic acids ( "AGS") available in large quantities as a by-product of the adipic acid preparation, a monomer used in the manufacture of polyamide or polyurethane.
- ASS Adipic, Glutaric and Succinic acids
- the mixture of diacids or diesters obtained from the mixture of diacids can be a raw material of particular interest from an economic, industrial and environmental point of view because a by-product is used and the use of resources is optimized.
- the groups R 2 , R 3 , R 4 and R 5 which are identical or different, are groups chosen from hydrocarbon groups comprising an average number of carbon atoms ranging from 1 to 36, saturated or unsaturated, linear or branched, optionally cyclic, optionally aromatic, optionally substituted, R 2 and R 3 on the one hand and R 4 and R 5 on the other hand may optionally together form a ring, optionally substituted and / or optionally comprising a heteroatom.
- the ring typically comprises the nitrogen atom to which R 2 and R 3 or R 4 and R 5 are linked.
- the cycle may comprise an additional heteroatom.
- the substituent may be a hydroxy group.
- the pairs R 2 and R 3 on the one hand and R 4 and R 5 on the other hand are identical pairs.
- R 2 and R 3 are identical.
- R 4 and R 5 are identical.
- R 2 , R 3 , R 4 and R 5 are identical
- the groups R 2 , R 3 , R 4 and R 5 which are identical or different, are chosen from methyl, ethyl, propyl (n-propyl), isopropyl, n-butyl, isobutyl and n-pentyl groups. , amyl, isoamyl, hexyl, cyclohexyl, hydroxyethyl.
- the groups R 2 and R 3 may also be such that together they form with the nitrogen atom a morpholine, piperazine or piperidine group.
- the product of the invention may comprise at least 10% by weight, preferably at least 50% by weight, preferably at least 75%, for example at least 95%, of the compounds of formulas (Ia), ( Ib) and (Ic).
- the product may be an ingredient or aid to processes intended to be combined with other ingredients or to be carried out in the presence of other chemical compounds.
- the product may be a composition or formulation comprising other ingredients.
- compounds (Ia), (Ib) and (Ic) can be introduced separately into the product. However, it is preferred to introduce them as a mixture or premix. According to a preferred embodiment the product is derived from a mixture wherein the compounds (Ia), (Ib) and (Ic) are present.
- the product may in particular be a product for amidification or trans-amidification.
- the product of the invention advantageously has a melting point less than or equal to 35 ° C, preferably less than or equal to 25 ° C, preferably less than or equal to 10 ° C, preferably less than or equal to 0 ° C.
- the product of the invention can be prepared by any suitable method. It is particularly preferred to carry out amidification or trans-amidification reactions on diacids or similar diesters, preferably in analogous mixtures. Such reactions are known to those skilled in the art.
- a suitable method for preparing a product of the invention may be a process comprising a step of amidification or trans-amidification with a compound of formula R 2 R 3 NH and / or HNR 4 R 5 of a mixture at least two compounds, preferably all three, chosen from the following compounds of formulas (a), (I'b) and (I'c): R 8 OOC-A a -COO R 8 (I'a) R 8 OOC-A b -COO R 8 (I'b) R 8 OOC-A c -COO R 8 (I'c) where R 8 is a hydrogen atom or a C 1 -C 6 alkyl, preferably a methyl.
- the compounds of formulas (a), (I'b), and (I'c) are considered analogous diacids or diesters respectively diamide compounds.
- the amidification or trans-amidating reaction can be carried out continuously, semi-continuously, or batchwise.
- conversion rate of the reaction conversion rate of the acid or diesters
- conversion rate of the acid or diesters conversion rate of the acid or diesters
- conversion rate of the acid or diesters conversion rate of the acid or diesters
- the alcohols formed during a trans-amidification reaction can be removed by stripping. It is noted that it is possible to use a very large excess of amine, an amine salt or any other means known to those skilled in the art, for example described in the book " March's Advanced Organic Chemistry "by Michael B. Smith and Jerry March, 5th Edition, John Wiley & Sons, pages 506-511 .
- the reaction may be followed by filtration and / or purification steps, for example by distillation.
- amidification or trans-amidating reaction can pass through activated intermediates such as the acid chlorides obtained, for example, from the compounds of formulas (a), (I'b), (I c) by reaction with thionyl chloride.
- activated intermediates such as the acid chlorides obtained, for example, from the compounds of formulas (a), (I'b), (I c) by reaction with thionyl chloride.
- the separation of the hydrochloric acid by-product during this type of amidification reaction, the reaction medium by any suitable means (salt formation, distillation), is a motor for moving the reaction equilibrium towards the formation of amide sought.
- the diacids or diesters in the form of mixtures may especially be mixtures of diacids derived from the manufacture of adipic acid (so-called AGS mixture) or diesters obtained from these diacid mixtures. Mixtures of diesters are in particular marketed under the name Rhodiasolv® RPDE.
- the product of the invention may especially be used as a solvent, co-solvent and / or crystallization inhibitor, as a plasticizer or as a coalescing agent.
- co-solvent is meant that other solvents may be associated with it.
- the use as a solvent or co-solvent includes the use to dissolve a compound in a formulation, in a reaction medium, the use to solubilize totally or partially a product to be removed (degreasing, stripping), and / or or to facilitate take-off of material films.
- the product of the invention may especially be used, for the functions indicated above or for others, in a phytosanitary formulation, in a cleaning formulation, in a pickling formulation, in a degreasing formulation, in a formulation lubricants or textiles, in a coating formulation, for example in a paint formulation, in a pigment formulation or ink, in a plastic formulation.
- the product may for example be used as a coalescing agent in an aqueous paint formulation.
- the product can in particular be used as a resin solvent, for example in the cable coating industry or in the electronics industry, especially as a solvent for PVDF.
- the product can be used as a cleaning and / or pickling solvent in the electronics industry. It can especially be used in lithium batteries. It can especially be used on photoresistant resins, polymers, waxes, fats, oils.
- the product can in particular be used for cleaning inks, for example during the production of inks or when printing ink is used.
- the product can especially be used for cleaning sieves or other tools used in manufacturing processes and / or recycling paper.
- the product can in particular be used for the cleaning of bitumen or tar sand, for example on coated substrates, on the tools used to apply these materials, on contaminated clothing, on soiled vehicles.
- the product can especially be used for cleaning flying machines such as airplanes, helicopters, space shuttles.
- the product may especially be used as a degreasing agent on metal surfaces, for example surfaces of tools, manufactured articles, sheets, molds, in particular steel or aluminum or alloys of these metals.
- the product can be used as a cleaning solvent on hard surfaces or textile surfaces.
- the product can in particular be used as a solvent for stripping paint or resins, on tool surfaces, for example foundry molds, on surfaces of industrial sites (floors, partitions, etc.).
- the paint stripping formulations may in particular be aqueous-based formulations (the compound being in admixture with water) or solvent-based (the compound then being the solvent or a compound mixed with water).
- the product can in particular be used as a plasticizer in thermoplastic polymer formulations.
- the cleaning and / or degreasing formulations may in particular be formulations for household care, operated in homes or in public areas (hotels, offices, factories, etc.). These can be formulations for cleaning hard surfaces such as floors, furniture and equipment surfaces in kitchens and bathrooms, and dishes. These formulations can also be used in the industrial sphere to degrease manufactured products and / or cleaned. Such formulations may in particular be used to clean and / or strip products, tools, molds, clothes or other.
- the product of the invention may especially be used in phytosanitary formulations comprising a solid active product. More details are given below, where the word “solvent” may refer to the product of the invention.
- Diacid diesters (“DiBasic Esters”) are also mentioned, in particular those marketed by Rhodia under the trade names Rhodiasolv RPDE and Rhodiasolv DIB. Also mentioned are hydrocarbon cuts, cyclic amides such as NMP, lactones. The bis (dialkylamides) which are the subject of the document WO 2008 // 074837 .
- the phytosanitary formulation is generally a concentrated phytosanitary formulation comprising an active compound.
- the phytosanitary formulations must allow easy weight dilution by the farmer, in order to obtain a product in which the phytosanitary product is correctly dispersed, for example in the form of a solution, emulsion, suspension, or suspension. emulsion.
- the phytosanitary formulations thus allow the transport of a phytosanitary product in relatively concentrated form, easy packaging and / or easy handling for the end user.
- Different types of phytosanitary formulations can be used depending on the different plant protection products.
- Emulsifiable concentrates Emulsifiable Concentrates “EC”
- EW concentrated emulsions
- ME microemulsions
- WP wettable powders
- WDG Water Dispersible Granules
- the formulations that can be used depend on the physical form of the phytosanitary product (for example solid or liquid), and its physico-chemical properties in the presence of other compounds such as water or solvents.
- the phytosanitary product may be in various physical forms: solution, dispersion of solid particles, dispersion of droplets of the product, droplets of solvent in which the product is dissolved ...
- the formulations Phytosanitary products generally include compounds that make it possible to obtain these physical forms. It may for example be surfactants, solvents, mineral carriers, and / or dispersants. Often these compounds do not have an active character, but a character of intermediary for formulation aid.
- the phytosanitary formulations may in particular be in liquid form, or in solid form.
- the phytosanitary formulation thus comprises a solution of the product in the solvent.
- the formulation may be in solid form, for example in the form of a wettable powder (WP) in which the solution soaks an inorganic support, for example kaolin and / or silica.
- WP wettable powder
- the formulation may alternatively be in liquid form, for example in the form of an emulsifiable concentrate (EC) having a single clear liquid phase comprising the solvent and the product in solution, capable of forming an emulsion by adding water, without stirring or with a weak agitation.
- EC emulsifiable concentrate
- EW concentrated emulsion
- ME clear microemulsion
- tebuconazole is a particularly effective and widely used fungicide for soybean cultivation in particular.
- Crystals can have negative effects, including clogging the filters of the devices used to spread the diluted composition, clog the spray devices, decrease the overall activity of the formulation, create unnecessary problems of waste streams to remove the crystals, and / or cause a bad distribution of the active product on the agricultural field.
- Active plant protection products especially non-water soluble and solid products are known to those skilled in the art.
- the active plant protection product may in particular be a herbicide, an insecticide, an acaricide, a fungicide, or a rodent killing agent ("rodenticide" in English) for example a rat poison.
- suitable active ingredients mention may be made, inter alia, of Amtretryne, Diuron, Linuron, Chlortoluron, Isoproturon, Nicosulfuron, Metamitron, Diazinon, Aclonifen and Atrazine.
- Chlorothalonil Bromoxynil, Bromoxynil heptanoate, Bromoxynil octanoate, Mancozeb, Maneb, Zineb, Phenmedipham, Propanyl, phenoxyphenoxy series, heteroaryloxyphenoxy series, CMPP, MCPA, 2,4 -D, Simazine, the active products of the imidazolinones series, the organophosphorus family, with in particular Azinphos-ethyl, Azinphos-methyl, Alachlor, Chlorpyriphos, Diclofop-methyl, Fenoxaprop-p Methyl Chlorine, Methoxychlor, Cypermethrin, Fenoxycarb, Cymoxanil, Chlorothalonyl, neonicotinoid insecticides, triazole fungicide family such as azaconazole, bromuconazole, cyproconazole, difenoconazole, dini
- active plant protection products may be used: Alachlor, Chlorpyrifos, alpha-cypermethrin, Phenmedipham, Propanil, Pendimethalin, Triadimenol, Trifluralin, Oxyfluorfen, Dimethoate, Imidacloprid, Proxopur, Benomyl, Deltamethrin, Fenvalerate, Abamectin, Amicarbazone, Bifenthrin, Carbosulfan, Cyfluthrin, Difenconazole, Ethofenprox, Fenoxaprop-ethyl, Fipronil, Fenvalerate, Fluazifop-p-butyl, Flufenouron, Hexazinone, Lambda-cyalothrin, Methomyl, Permethrin, Prochloraz, Propiconazole, Tebuconazole
- the phytosanitary formulation may comprise an emulsifying agent, typically and preferably a surfactant.
- the emulsifying agents are agents intended to facilitate the emulsification or dispersion after placing the formulation in contact with water, and / or to stabilize (in time and / or in temperature) the emulsion or the dispersion. for example by avoiding sedimentation.
- Surfactants are known compounds, which have a generally relatively low molar mass, for example less than 1000 g / mol.
- the surfactant can be an anionic surfactant in salified or acidic form, preferably polyalkoxylated nonionic, cationic, amphoteric (term also including zwitterionic surfactants). It may be a mixture or combination of these surfactants.
- the anionic surfactants can be in acid form (they are potentially anionic), or in partially or totally salified form, with a counterion.
- the counterion may be an alkali metal, such as sodium or potassium, an alkaline earth metal, such as calcium, or an ammonium ion of formula N (R) 4 + in which R, identical or different, represent a hydrogen atom or a C 1 -C 4 alkyl radical optionally substituted with an oxygen atom.
- the formulation advantageously comprises at least 4%, preferably at least 5%, preferably at least 8%, by weight of dry matter, of at least one surfactant c).
- the solvent may be combined with an aromatic and / or nonaromatic surfactant.
- the phytosanitary formulation preferably does not include significant amounts of water.
- the water content is less than 50% by weight, preferably less than 25% by weight. It will generally be less than 10% by weight.
- the formulation is preferably a liquid formulation, for example in the form of an emulsifiable concentrate (EC), a concentrated emulsion (EW) or a micoremulsion (ME).
- EC emulsifiable concentrate
- EW concentrated emulsion
- ME micoremulsion
- it preferably comprises less than 500 g / l of water, more preferably less than 250 g / l. It will generally be less than 100 g / L.
- solid formulations for example formulations in which a liquid comprising the phytosanitary product solubilized in the solvent, is supported by a mineral and / or dispersed in a solid matrix.
- the formulation may of course include other ingredients (or "other additives") than the active plant protection product, the solvent (s), the optional emulsifying agent (s) and the optional water. It may especially comprise viscosity modifiers, defoamers, especially silicone antifoams, anti-rebound agents, anti-leaching agents, inert fillers, in particular mineral fillers, anti-freeze agents, etc.
- the concentrated phytosanitary formulation is intended to be spread over a cultivated field or to be cultivated, for example a soybean field, most often after dilution in water, to obtain a diluted composition.
- Dilution is generally carried out by the farmer, directly in a tank ("tank-mix"), for example in the tank of a device for spreading the composition. It is not excluded that the operator adds other phytosanitary products, for example fungicides, herbicides, pesticides, insecticides, fertilizers.
- the formulation can be used to prepare a composition diluted in the water of the active plant protection product, by mixing at least one part by weight of concentrated formulation with at least 10 parts of water, preferably less than 1000 parts. Dilution rates and amounts to be applied in the field usually depend on the crop product and the desired dose to treat the field; this can be determined by the farmer.
- Diamide mixtures are prepared from diacid mixtures.
- the mixture of diacids and thionyl chloride are mixed at room temperature.
- the reaction mixture can be refluxed to complete the reaction.
- the volatile species are removed by distillation under reduced pressure to obtain the crude product which is typically used as such without further purification.
- Procedure B Formation of diamide (as a mixture) by reaction with a dialkylamine
- Toluene and triethylamine are charged and cooled to -10 ° C.
- the dialkylamine is then charged in liquid form.
- the acid dichloride (as a mixture), diluted in toluene, is then slowly added while maintaining the temperature below + 10 ° C.
- the mixture is then stirred for two hours at room temperature.
- the salts formed during the reaction are then filtered and washed with ethyl acetate.
- the filtrate thus obtained is evaporated on a rotary evaporator to obtain the crude reaction.
- the final product is finally obtained after distillation under reduced pressure.
- Example 1.1 Preparation of a product comprising a mixture of the following compounds:
- the product is observed at different temperatures. It is found to be liquid at temperatures of 35 ° C, 30 ° C, 25 ° C, 20 ° C, 10 ° C. It is also found that it is free of crystals at these temperatures.
- Dialkyl diamide (as a mixture) is obtained by Procedure B.
- Gross product 1068 g (brown liquid)
- Final product 700 g (slightly yellow liquid)
- the product obtained is analyzed by gas chromatography.
- the analysis indicates (in peak area): And 2 NOC-CH 2 -CH 2 -CONEt 2 13.09% And 2 NOC-CH 2 -CH 2 -CH 2 -CONEt 2 70.60% And 2 NOC-CH 2 -CH 2 - CH 2 -CH 2 -CONE 2 12.71%
- the product is observed at different temperatures. It is found to be liquid at temperatures of 35 ° C, 30 ° C, 25 ° C, 20 ° C, 10 ° C, 0 ° C, -10 ° C. It is also found that it is free of crystals at these temperatures.
- Examples 2 are comparative examples in which the product Rhodiasolv® ADMA10, Rhodia (Asia-Pacific zone) is used as solvent: Alkydimethylamide solvent.
- the following EC formulation is prepared: Imidacloprid tech.98% 204 g / L Solvent of Example 1.1 856 g / L Soprophor® 769 / P (surfactant, Rhodia) 150 g / L
- the properties of the formulation are evaluated after 14 days at 54 ° C: - pH (Cipoac MT 75 method): 3.0 - Emulsification (Cipac test, at 0.5% concentration at 30 ° C, after 2 hours AT D VS 0t 0 0
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Claims (11)
- Erzeugnis umfassend mindestens zwei Diamid-Verbindungen ausgewählt aus den Diamid-Verbindungen der folgenden Formeln (Ia), (Ib) und (Ic):
R2R3NOC-Aa-CONR4R5 (Ia)
R2R3NOC-Ab-CONR4R5 (Ib)
R2R3NOC-Ac-CONR4R5 (Ic)
wobei:- R2, R3, R4 und R5, identisch oder verschieden, ausgewählt sind aus Methyl-, Ethyl-, Propyl- (n-Propyl-), Isopropyl-, n-Butyl-, Isobutyl-, n-Pentyl, Amyl-, Isoamyl-, Hexyl-, Cyclohexyl-, Hydroxyethyl-, Morpholin-, Piperazin- oder Piperidingruppen;- Aa die Gruppe der folgenden Formel -CH2-CH2- (Ethylen) ist,- Ab die Gruppe der folgenden Formel -CH2-CH2-CH2- (n-Propylen) ist, und- Ac die Gruppe der folgenden Formel -CH2-CH2-CH2-CH2- (n-Butylen) ist. - Erzeugnis gemäß einem der vorangehenden Ansprüche, gekennzeichnet dadurch, dass es die drei Verbindungen der Formeln (Ia), (Ib) und (Ic) umfasst.
- Erzeugnis gemäß einem der vorangehenden Ansprüche, gekennzeichnet dadurch, dass es im Verhältnis zur absoluten Molzahl der Diamide der Formeln (Ia), (Ib) und (Ic):- von 1 bis 20 Mol-%, vorzugsweise von 5 bis 15 Mol-% an Diamid der Formel (Ic),- von 45 bis 75 Mol-%, vorzugsweise von 55 bis 65 Mol-% an Diamid der Formel (Ib) und- von 15 bis 45 Mol-%, vorzugsweise von 20 bis 33 Mol-% an Diamid der Formel (Ia)
umfasst. - Erzeugnis gemäß einem der vorangehenden Ansprüche, gekennzeichnet dadurch, dass:- die Verbindung der Formel (Ia) die Verbindung Me2NOC-CH2-CH2-CONMe2 ist,- die Verbindung der Formel (Ib) die Verbindung Me2NOC-CH2-CH2-CH2-CONMe2 ist, und- die Verbindung der Formel (Ic) die Verbindung Me2NOC-CH2-CH2-CH2-CH2-CONMe2 ist.
- Erzeugnis gemäß einem der Ansprüche 1 bis 3, gekennzeichnet dadurch, dass:- die Verbindung der Formel (Ia) die Verbindung Et2NOC-CH2-CH2-CONEt2 ist,- die Verbindung der Formel (Ib) die Verbindung Et2NOC-CH2-CH2-CH2-CONEt2 ist, und- die Verbindung der Formel (Ic) die Verbindung Et2NOC-CH2-CH2-CH2-CH2-CONEt2 ist.
- Erzeugnis gemäß einem der vorangehenden Ansprüche, gekennzeichnet dadurch, dass es mindestens 10 Gew.-%, vorzugsweise mindestens 50 Gew.-% an Verbindungen der Formeln (Ia), (Ib) und (Ic) umfasst.
- Erzeugnis gemäß Anspruch 6, gekennzeichnet dadurch, dass es ein Amidierungsprodukt oder ein trans-Amidierungsprodukt ist.
- Erzeugnis gemäß einem der vorangehenden Ansprüche, gekennzeichnet dadurch, dass es eine Schmelztemperatur von weniger als oder gleich 35 °C, vorzugsweise weniger als oder gleich 25 °C, vorzugsweise weniger als oder gleich 10 °C, vorzugsweise weniger als oder gleich 0 °C aufweist.
- Verfahren zur Herstellung eines Erzeugnisses gemäß einem der vorangehenden Ansprüche, umfassend einen Amidierungs- oder trans-Amidierungsschritt einer Verbindung der Formel R2R3NH und/oder HNR4R5 einer Mischung von mindestens zwei Verbindungen ausgewählt aus den Verbindungen der folgenden Formeln (I'a), (I'b) und (I'c):
R8OOC-Aa-COO R8 (I'a)
R8OOC-Ab-COO R8 (I'b)
R8OOC-Ac-COO R8 (I'c)
wobei R8 ein Wasserstoffatom oder ein C1-C6-Akyl ist, vorzugsweise ein Methyl. - Verwendung eines Erzeugnisses, wie in einem der Ansprüche 1 bis 8 definiert, als Lösemittel, Weichmacher oder Koaleszenzmittel.
- Verwendung eines Erzeugnisses, wie in einem der Ansprüche 1 bis 8 definiert, in einer Pflanzenschutzmittelformulierung, in einer Reinigungsformulierung, in einer Beizformulierung, in einer Entfettungsformulierung, in einer Schmiermittelformulierung, in einer Beschichtungsformulierung, in einer Pigment- oder Tintenformulierung, oder in einer Kunststoffformulierung.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0805188A FR2936129B1 (fr) | 2008-09-22 | 2008-09-22 | Produit comprenant des diamides, procede de preparation et utilisations |
PCT/EP2009/062208 WO2010031867A1 (fr) | 2008-09-22 | 2009-09-21 | Produit comprenant des diamides, procede de preparation et utilisations |
Publications (2)
Publication Number | Publication Date |
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EP2328862A1 EP2328862A1 (de) | 2011-06-08 |
EP2328862B1 true EP2328862B1 (de) | 2015-10-21 |
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ID=40568776
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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EP09783247.1A Active EP2328862B1 (de) | 2008-09-22 | 2009-09-21 | Diamide enthaltendes produkt, verfahren zu dessen herstellung und anwendungen davon |
Country Status (6)
Country | Link |
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US (1) | US20120029092A1 (de) |
EP (1) | EP2328862B1 (de) |
AR (1) | AR075276A1 (de) |
ES (1) | ES2557597T3 (de) |
FR (1) | FR2936129B1 (de) |
WO (1) | WO2010031867A1 (de) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
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EP2364591A1 (de) * | 2010-03-09 | 2011-09-14 | Cognis IP Management GmbH | Biozidzusammensetzungen, die Dicarbonsäurealkylamide umfassen |
US20200181065A1 (en) | 2016-04-06 | 2020-06-11 | Rhodia Operations | N-alkyldiamide compounds and gels comprising the same |
EP3466398A1 (de) | 2017-10-05 | 2019-04-10 | Rhodia Operations | N-hydrocarbyldiamid-zusammensetzung mit gelierenden eigenschaften |
WO2019068914A1 (en) | 2017-10-05 | 2019-04-11 | Rhodia Operations | FORMULATIONS COMPRISING SURFACTANTS, ORGANIC LIQUIDS AND VISCOSITY IMPROVERS |
WO2019068913A1 (en) | 2017-10-05 | 2019-04-11 | Rhodia Operations | FORMULATIONS COMPRISING BIOLOGICALLY ACTIVE PRINCIPLES |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3632783A (en) * | 1969-05-27 | 1972-01-04 | Hall Co C P | Treatment of mosquito bites employing certain tetraalkyl diamides |
JPS57154102A (en) * | 1981-03-19 | 1982-09-22 | Takako Mori | Insecticidal method |
ATE14364T1 (de) * | 1981-11-07 | 1985-08-15 | Siegfried Ag | Verfahren zur bekaempfung eines breiten spektrums von unkraeutern in kulturen und zusammensetzung fuer dieses verfahren. |
EP0143303A3 (de) | 1983-10-29 | 1986-04-30 | Bayer Ag | Verfahren zur Herstellung von substituierten Bernsteinsäureamiden |
CA1294981C (en) | 1984-11-29 | 1992-01-28 | Robert A. Dubbert | 1,6 hexanediamides from 3-pentenamides |
DE4404222A1 (de) * | 1994-02-10 | 1995-08-17 | Bayer Ag | Verwendung von Dicarbonsäure-bis-dimethylamiden als Kristallisationsinhibitoren |
UA52701C2 (uk) * | 1996-10-11 | 2003-01-15 | Басф Акцієнгезельшафт | Твердий засіб захисту рослин та спосіб його одержання, спосіб боротьби з небажаним ростом рослин, спосіб боротьби з шкідливими грибами і тваринами-шкідниками та спосіб регулювання росту рослин |
US6391451B1 (en) * | 1999-09-07 | 2002-05-21 | Basf Aktiengesellschaft | Surface-treated superabsorbent polymer particles |
FR2872824B1 (fr) * | 2004-07-06 | 2006-09-22 | Rhodia Chimie Sa | Procede pour epaissir un milieu liquide concentre en agents tensioactifs |
FR2910000B1 (fr) * | 2006-12-19 | 2009-10-16 | Rhodia Recherches & Tech | Nouveaux composes bis(dialkylamides), procede de preparation et utilisations. |
-
2008
- 2008-09-22 FR FR0805188A patent/FR2936129B1/fr not_active Expired - Fee Related
-
2009
- 2009-09-21 WO PCT/EP2009/062208 patent/WO2010031867A1/fr active Application Filing
- 2009-09-21 EP EP09783247.1A patent/EP2328862B1/de active Active
- 2009-09-21 ES ES09783247.1T patent/ES2557597T3/es active Active
- 2009-09-21 US US13/120,374 patent/US20120029092A1/en not_active Abandoned
- 2009-09-22 AR ARP090103625A patent/AR075276A1/es not_active Application Discontinuation
Also Published As
Publication number | Publication date |
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AR075276A1 (es) | 2011-03-23 |
FR2936129A1 (fr) | 2010-03-26 |
FR2936129B1 (fr) | 2012-10-12 |
EP2328862A1 (de) | 2011-06-08 |
WO2010031867A1 (fr) | 2010-03-25 |
US20120029092A1 (en) | 2012-02-02 |
ES2557597T3 (es) | 2016-01-27 |
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